2-(N-Acyl) and 2-N-acyl-N6-substituted analogues of adenosine and their affinity at the human adenosine receptors

Prakash G. Jagtap, Zhiyu Chen, Csaba Szabo, Karl Norbert Klotz

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Abstract

A series of 2-(N-acyl) and 2-(N-acyl)-N6-alkyladenosine analogues have been synthesized from the intermediate 2-amino-6-chloroadenosine derivatives (2b and 7) and evaluated for their affinity at the human A 1, A2A, and A3 receptors. We found that 2-(N-acyl) derivatives of adenosine showed relatively low affinity at A 2A and A3 receptors, while the N6-cyclopentyl substituent in 4h and 4i induced high potency [A1 (K i)=20.7 and 31.8 nM respectively] at the A1 receptor and resulted therefore in increased selectivity for this subtype. The general synthetic methods and their binding studies are presented herein.

Original languageEnglish (US)
Pages (from-to)1495-1498
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume14
Issue number6
DOIs
StatePublished - Mar 22 2004
Externally publishedYes

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Purinergic P1 Receptors
Adenosine
Derivatives

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

2-(N-Acyl) and 2-N-acyl-N6-substituted analogues of adenosine and their affinity at the human adenosine receptors. / Jagtap, Prakash G.; Chen, Zhiyu; Szabo, Csaba; Klotz, Karl Norbert.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 14, No. 6, 22.03.2004, p. 1495-1498.

Research output: Contribution to journalArticle

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